Sodium Hydroxide → 5-[Bis-(2,2,2-trifluoro-ethyl)-amino]-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

HRID 632220Notes

Reaction equation

HRID 632220 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:12][C:13]([F:16])([F:15])[F:14])=[C:7]([O:22][CH2:23][CH:24]2[CH2:26][CH2:25]2)[N:6]=1)=[O:4].[OH-].[Na+]>C(O)C>[F:21][C:18]([F:19])([F:20])[CH2:17][N:11]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=1[O:22][CH2:23][CH:24]1[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866747735-(Bis(2,2,2-trifluoroethyl)amino)-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 866747745-[Bis-(2,2,2-trifluoro-ethyl)-amino]-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(bis(2,2,2-trifluoroethyl)amino)-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid methyl ester (60 mg, 0.16 mmol) and sodium hydroxide (9 mg, 0.23 mmol) in ethanol (20 mL) was reacted for 2 h at 90° C. The reaction mixture was concentrated under reduced pressure, dissolved in water and extracted with ethyl acetate (10 mL). The pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid; the aqueous layer was extracted with ethyl acetate (3×10 mL), washed with brine (2×10 mL), dried over Na2SO4 and evaporated to dryness (0.03 g, crude). The crude product was used for next step without further purification; MS: m/e=373.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in water
  3. extractionextracted with ethyl acetate (10 mL)
  4. additionThe pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  6. washwashed with brine (2×10 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness (0.03 g, crude)
  9. customThe crude product was used for next step without further purification

Sources & evidence

ORD record
ord-441e6ec58ad04fa6bd465f1d98b245f7
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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